1. Field of the Invention
The present invention relates to crystalline and amorphous pyrimidine compounds, and processes for preparing the same. More particularly, the present invention relates to crystals (the crystal form C) of 5-[2-amino-4-(2-furyl)pyrimidin-5-yl]-1-methylpyridin-2(1H)-one, a compound effective for prevention and treatment for various diseases such as constipation, and processes for preparing the same; crystals of 5-[2-amino-4-(2-furyl)pyrimidin-5-yl]-1-methylpyridin-2(1H)-one hydrate and processes for preparing the same; and amorphous 5-[2-amino-4-(2-furyl)pyrimidin-5-yl]-1-methylpyridin-2(1H)-one and processes for preparing the same. The present invention relates also to processes for preparing pyrimidine compounds such as 5-[2-amino-4-(2-furyl)pyrimidin-5-yl]-1-methylpyridin-2(1H)-one and intermediates thereof.
2. Related Background of the Invention
5-[2-Amino-4-(2-furyl)pyrimidin-5-yl]-1-methylpyridin-2(1H)-one is a compound having adenosine receptor antagonism and being effective for prevention and treatment for various diseases such as constipation (see patent document 1). Patent document 1, Example 16 discloses 5-[2-amino-4-(2-furyl)pyrimidin-5-yl]-1-methylpyridin-2(1H)-one was obtained as crystals.
The process for preparing 5-[2-amino-4-(2-furyl)pyrimidin-5-yl]-1-methylpyridin-2(1H)-one disclosed in patent document 1 is, as shown in the reaction scheme below, a method of allowing 2-(6-chloro-3-pyridyl)-3-dimethylamino-1-(2-furyl)-2-propene-1-one to react with guanidine to afford 5-(6-chloro-3-pyridyl)-4-(2-furyl)-2-pyrimidinylamine, oxidizing this to afford 5-[2-amino-4-(2-furyl)-5-pyrimidinyl]-1,2-dihydro-2-pyridinone, and then methylating this.

Also is disclosed in patent document 1, a method of acidizing 5-(6-benzyloxy-3-pyridyl)-4-(2-furyl)-2-pyrimidinylamine to afford 5-[2-amino-4-(2-furyl)-5-pyrimidinyl]-1,2-dihydro-2-pyridinone.

Furthermore, the following reaction is described as general production method D in patent document 1.

In the above formula, R1d represents a C6-14 aromatic hydrocarbon ring group, a 5- to 14-membered aromatic heterocyclic group, etc., but the reaction in which R1d is N-alkyl pyridone is not specifically disclosed.
Patent Document 1: WO 03/035639